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Columbin Sale

(Synonyms: 古伦宾) 目录号 : GC31749

A diterpenoid furanolactone with diverse biological activities

Columbin Chemical Structure

Cas No.:546-97-4

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10mM (in 1mL DMSO)
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5mg
¥446.00
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10mg
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25mg
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50mg
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实验参考方法

Animal experiment:

Rats: Male Wistar rats are treated as following: i.v. injection of columbin in EtOH and PEG-300 (1:1) is administrated through tail vein at dose of 20 mg/kg. Intraperitoneal (i.p.) injection of columbin in EtOH and PEG-300 (1:1) is administrated at dose of 20 mg/kg. An oral gavage of columbin suspended in oral suspension vehicle is given to rats at dose of 50 mg/kg. Blood samples (50-100 μL) are collected by snipping the tail into heparinized tubes at 0, 5, 15, 30, 45, 60, 120, 240, 360, 480 and 1440 min for i.v. administration, or at 0, 15, 30, 60,120, 180, 240, 360, 480, 1440 min for oral dosing or i.p. injection. The blood samples are stored at −20°C until analysis[2]. Mice: Male Balb/c mice (n=60) are randomly divided into six groups. Columbin is intra-peritoneally administered to mice at the dose of 30, 100, 300 and 700 mg/kg. Aspirin, an anti-inflammatory drug, is used as a positive control. To induce acute phase inflammation in paw, rats are injected subcutaneously into the right hind paw with a 1% solution of carrageenan dissolved in saline 30 min after vehicle or columbin treatment. The paw volumes are measured up to 5 h after the injection at intervals of 1 h. Paw volume is measured with a plethysmometer immediately prior to the injection of carrageenan and thereafter at an interval of 1 h for a period of 5 h[1].

References:

[1]. Ibrahim Abdelwahab S, et al. In vitro and in vivo anti-inflammatory activities of columbin through the inhibition of cycloxygenase-2 and nitric oxide but not the suppression of NF-κB translocation. Eur J Pharmacol. 2012 Mar 5;678(1-3):61-70.
[2]. Yang G, et al. Development and validation of an UPLC-MS/MS method for the quantification of columbin in biological matrices: Applications to absorption, metabolism, and pharmacokinetic studies. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:13-8.

产品描述

Columbin is a diterpenoid furanolactone isolated from J. columba, A. albida, and T. bakis that has diverse biological activities.1,2,3,4 It inhibits the growth of T. brucei in vitro and induces complete parasite clearance in T. brucei-infected mice when administered at a dose of 25 mg/kg per day for three days.1 Columbin selectively inhibits COX-2 over COX-1 (EC50s = 53.1 and 327 μM, respectively) and reduces carrageenan-induced paw edema in rats in a dose-dependent manner.2 Dietary feeding of columbin (4, 20, and 100 ppm) reduces the number of lesions in a rat model of azoxymethane-induced colon carcinogenesis.3 Columbin (20-40 mg/kg per day) also reduces sleeping time induced by a mixture of urethane and α-choralose but prolongs sleeping time induced by hexobarbital in mice.4

1.Nok, A.J., Sallau, B.A., Onyike, E., et al.Columbin inhibits cholesterol uptake in bloodstream forms of Trypanosoma brucei-A possible trypanocidal mechanismJ. Enzyme Inhib. Med. Chem.20(4)365-368(2005) 2.Abdelwahab, S.I., Koko, W.S., Mohamed Elhassan Taha, M., et al.In vitro and in vivo anti-inflammatory activities of columbin through the inhibition of cycloxygenase-2 and nitric oxide but not the suppression of NF-κB translocationEur. J. Pharmacol.678(1-3)61-70(2012) 3.Kohno, H., Maeda, M., Tanino, M., et al.A bitter diterpenoid furanolactone columbin from Calumbae Radix inhibits azoxymethane-induced rat colon carcinogenesisCancer Lett.183(2)131-139(2002) 4.Wada, K., Kurihara, T., Yagi, M., et al.Columbin isolated from calumbae radix affects the sleeping time of anesthetized miceBiol. Pharm. Bull.18(4)634-636(1995)

Chemical Properties

Cas No. 546-97-4 SDF
别名 古伦宾
Canonical SMILES O=C1[C@](C=C2)(O)[C@@](CC3)(C)[C@@]([C@@](C[C@@H](C4=COC=C4)O5)(C)[C@]3([H])C5=O)([H])[C@]2([H])O1
分子式 C20H22O6 分子量 358.39
溶解度 DMSO : ≥ 100 mg/mL (279.03 mM);Water : < 0.1 mg/mL (insoluble) 储存条件 Store at -20°C
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1 mM 2.7903 mL 13.9513 mL 27.9026 mL
5 mM 0.5581 mL 2.7903 mL 5.5805 mL
10 mM 0.279 mL 1.3951 mL 2.7903 mL
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Research Update

Cytochrome P450 Enzyme-Mediated Bioactivation as an Underlying Mechanism of Columbin-Induced Hepatotoxicity

Columbin, a furanoid compound, is the major bioactive ingredient of Tinospora sagittata (Oliv.) Gagnep, a traditional Chinese medicine that has been reported to cause liver injury in the clinic. The aim of this study was to investigate the hepatotoxicity caused by columbin and its underlying mechanism. Our results indicated that columbin could result in a dose-dependent increase of mice serum alanine aminotransferase and aspartate aminotransferase after oral treatment with columbin, as well as local spotty necrosis in the liver of mice treated with columbin. No hepatotoxicity was observed in mouse treated with the same dose of tetrahydrocolumbin. Pretreatment with ketoconazole preserved the mice from columbin-induced hepatotoxicity. Further studies suggested that bioactivation of the furan ring played an indispensable role in columbin-caused hepatotoxicity. In vitro and in vivo metabolism studies demonstrated that columbin could be metabolized into the cis-butene-1,4-dial intermediate, which readily reacted with glutathione and N-acetyllysine to form stable adducts. Ketoconazole displayed strong inhibitory effect on the generation of M4 and M5 both in vitro and in vivo. Further recombinant human CYP450 screening demonstrated that CYP3A4 was the major enzyme responsible for columbin bioactivation. The present study demonstrated that columbin was hepatotoxic and CYP3A4-mediated bioactivation of the furan ring would serve as an underlying mechanism for columbin-induced hepatotoxicity.

In vitro and in vivo anti-inflammatory activities of columbin through the inhibition of cycloxygenase-2 and nitric oxide but not the suppression of NF-κB translocation

Columbin, a diterpenoid furanolactone, was isolated purely for the first time from the plant species Tinspora bakis. The anti-inflammatory effects of columbin were studied in vitro, in silico and in vivo. The effect of columbin on nitric oxide was examined on lipopolysaccharide-interferon-gamma (LPS/IFN) induced RAW264.7 macrophages. In vitro and in silico cyclooxygenase-1 and cyclooxygenase-2 inhibitory activities of columbin using biochemical kit and molecular docking, respectively, were investigated. Mechanism of columbin in suppressing NF-kappaB-translocation was tested using Cellomics?NF-κB activation assay and ArrayScan Reader in LPS-stimulated RAW264.7 cells. Moreover, effects of columbin in vivo that were done on carrageenan-induced mice paw-oedema were tested. Lastly, the in vitro and in vivo toxicities of columbin were examined on human liver cells and mice, respectively. Treatment with columbin or N(ω)-nitro-l-arginine methyl ester (l-NAME) inhibited LPS/IFN-γ-induced NO production without affecting the viability of RAW264.7. Pre-treatment of stimulated cells with columbin did not inhibit the translocation of NF-κB to the nucleus in LPS-stimulated cells. COX-1 and COX-2 inhibitory activities of columbin were 63.7±6.4% and 18.8±1.5% inhibition at 100μM, respectively. Molecular docking study further helped in supporting the observed COX-2 selectivity. Whereby, the interaction of columbin with Tyr385 and Arg120 signifies its higher activity in COX-2, as Tyr385 was reported to be involved in the abstraction of hydrogen from C-13 of arachidonate, and Arg120 is critical for high affinity arachidonate binding. Additionally, columbin inhibited oedema formation in mice paw. Lastly, the compound was observed to be safe in vitro and in vivo. This study presents columbin as a potential anti-inflammatory drug.

Method development and validation for quantification of six bioactive compounds (andrographolide, columbin, piperine, gallic, paracoumaric and oleanolic acids) by HPTLC

Objectives: During the spread of pandemic diseases, immunity boosting herbal drugs are taken as a preventive medicine. Kapacurak Ku?inīr Cūra?am is a Siddha drug used for flu like viral infections, cold and fever. Developing an analytical method to estimate the content of active phytoconstituents in such antiviral immune boosting drug will be useful in the phyto pharmaceutical industry.
Methods: A precise, reliable and sensitive ordinary phase high performance thin layer chromatography (HPTLC) method has been developed and validated for identification and simultaneous estimation of six bioactive components namely like andrographolide, columbin, gallic acid, ρ-coumaric acid, piperine and oleanolic acid from any Indian traditional medicine, medicinal plant, drugs and food materials etc. The separation was achieved on silica gel 60F254 TLC plates using toluene: ethyl acetate: formic acid (7:3:0.5, v/v) as mobile phase. The gallic acid, ρ-coumaric acid, piperine markers were estimated using the densitometric scanning in absorption mode at 254 nm. The densitometric scanning was done after derivatization (vanillin-sulphuric acid reagent) at λ=520 nm for andrographolide, columbin and oleanolic acid.
Results: The linear regression analysis data for the calibration plots showed a correlation coefficient in the concentration range 1-5 μg per band for the bioactive markers with respect to area. The method was validated for accuracy, precision, limit of detection (LOD), and quantitation of limit (LOQ).
Conclusions: Developed method was accurate, precise and fast to ensure the quality of Kapacurak Ku?inīr Cūra?am.

Semisynthesis and Kappa-Opioid Receptor Activity of Derivatives of Columbin, a Furanolactone Diterpene

Columbin (1) is a furanolactone diterpene isolated from the roots of Jateorhiza and Tinospora species. These species generally grow in Asia and Africa and have been used in folk medicine for their apparent analgesic and antipyretic activities. Columbin (1) is of particular interest due to its structural similarity to the known kappa-opioid receptor (KOR) agonist salvinorin A. Given that the KOR is of interest in the study of many serious diseases, such as anxiety, depression, and drug addiction, obtaining natural or semisynthetic molecules with KOR activity recently has gained much interest. For this reason, in the present study, derivatives of 1 were designed and synthesized using known structure-activity relationships of salvinorin A at KORs. The structures of the columbin analogues prepared were elucidated by NMR spectroscopy and mass spectroscopy, and their KOR activity was investigated in vitro by inhibition of forskolin-induced cAMP accumulation. Slight improvements in KOR activity were observed in columbin derivatives over their parent compound. However, despite the structural similarities to salvinorin A, neither columbin (1) nor its derivatives were potent KOR ligands. This work represents not only the first evaluation of columbin (1) at the KOR but also one of the first works to explore synthetic strategies that are tolerated on the columbin core.

Columbin inhibits cholesterol uptake in bloodstream forms of Trypanosoma brucei-A possible trypanocidal mechanism

The diterpenoid furanolactone (columbin) from Aristolochia albida inhibited growth of culture forms of Trypanosoma brucei. In vitro analysis of the compound at 5-250 microg/ml showed complete lysis of the parasites within 10-20 minutes post incubation. At 50 microg/ml, columbin killed about 50% of the parasites which initially appeared swollen under phase contrast microscopy. Also the total amount of cholesterol diminished dose-dependently in the presence of 10-100 microg/ml of columbin after a 3-day incubation period. In vivo analysis of the compound in T. brucei-infected mice revealed that 25 mg/kg administered for 3 consecutive days, completely cleared the parasites from the peripheral circulation. However, columbin could not clear parasites in the cerebrospinal fluid.